#------------------------------------------------------------------------------
#$Date: 2022-06-15 05:03:52 +0300 (Wed, 15 Jun 2022) $
#$Revision: 276036 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/71/1567118.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1567118
loop_
_publ_author_name
'Jirát, Jan'
'Babor, Martin'
'Ridvan, Luděk'
'Skořepová, Eliška'
'Dušek, Michal'
'Šoóš, Miroslav'
_publ_section_title
;
 Structure--property relations of a unique and systematic dataset of 19
 isostructural multicomponent apremilast forms
;
_journal_coeditor_code           ED5027
_journal_issue                   4
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052252522005577
_journal_volume                  9
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25.50 H25.50 N2 O8.50 S1'
_chemical_formula_sum            'C25.5 H25.5 N2 O8.5 S'
_chemical_formula_weight         528.06
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.90760(10)
_cell_length_b                   12.90760(10)
_cell_length_c                   29.4670(2)
_cell_measurement_reflns_used    42651
_cell_measurement_temperature    120
_cell_measurement_theta_max      67
_cell_measurement_theta_min      4
_cell_volume                     4909.38(6)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            84206
_diffrn_reflns_theta_full        67.760
_diffrn_reflns_theta_max         67.760
_diffrn_reflns_theta_min         3.739
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.664
_exptl_absorpt_correction_T_max  0.82
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2212
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.70
_refine_diff_density_min         -0.86
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 1790 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   -0.000(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0266
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4433
_refine_ls_number_restraints     62
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.0019124
_refine_ls_shift/su_mean         0.0001104
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.08P)² + 7.51P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1456
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1456
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              35
_reflns_limit_l_min              0
_reflns_number_gt                4320
_reflns_number_total             4433
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.15
_oxford_diffrn_Wilson_scale      0.10
_oxford_refine_ls_r_factor_ref   0.0513
_oxford_refine_ls_scale          3.27(6)
_oxford_reflns_number_all        4433
_cod_data_source_file            ed5027.cif
_cod_data_source_block           Apremilast_4_hydroxybenzoic_acid
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        4909.38(8)
_cod_original_sg_symbol_H-M      'P 41 21 2 '
_cod_original_formula_sum        'C25.50 H25.50 N2 O8.50 S1'
_cod_database_code               1567118
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_hooft_y                  -0.000(2)
_oxford_bijvoet_difference       -0.000(3)
_oxford_refined_flack_x          0.00(3)
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-y+1/2,x+1/2,z+1/4
-x,-y,z+1/2
x+1/2,-y+1/2,-z+3/4
-y,-x,-z+1/2
y+1/2,-x+1/2,z+3/4
y,x,-z
-x+1/2,y+1/2,-z+1/4
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.16345(7) 0.59577(7) 0.71378(3) 0.0259 1.0000 Uani . . . . . .
O2 O 0.0761(2) 0.5544(2) 0.68929(9) 0.0348 1.0000 Uani . . . . . .
O3 O 0.2117(2) 0.6883(2) 0.69586(9) 0.0331 1.0000 Uani . . . . . .
C4 C 0.1252(3) 0.6203(3) 0.76999(14) 0.0402 1.0000 Uani . . . . . .
C5 C 0.2590(3) 0.4986(3) 0.71999(11) 0.0245 1.0000 Uani . . . . . .
C6 C 0.2971(3) 0.4542(3) 0.67499(11) 0.0227 1.0000 Uani . . . . . .
C7 C 0.3061(3) 0.5631(3) 0.60378(11) 0.0223 1.0000 Uani . . . . . .
C8 C 0.3679(3) 0.6541(3) 0.58890(11) 0.0231 1.0000 Uani . . . . . .
C9 C 0.4391(3) 0.6770(3) 0.62254(11) 0.0248 1.0000 Uani . . . . . .
C10 C 0.4245(3) 0.6011(3) 0.65965(11) 0.0240 1.0000 Uani . . . . . .
O11 O 0.23506(18) 0.51937(19) 0.58418(8) 0.0267 1.0000 Uani . . . . . .
O12 O 0.47155(19) 0.5941(2) 0.69558(8) 0.0292 1.0000 Uani . . . . . .
C13 C 0.3636(3) 0.7094(3) 0.54847(11) 0.0235 1.0000 Uani . . . . . .
C14 C 0.4344(3) 0.7913(3) 0.54412(13) 0.0282 1.0000 Uani . . . . . .
C15 C 0.5040(3) 0.8140(3) 0.57841(13) 0.0315 1.0000 Uani . . . . . .
C16 C 0.5091(3) 0.7566(3) 0.61870(12) 0.0291 1.0000 Uani . . . . . .
N17 N 0.2920(2) 0.6786(2) 0.51553(10) 0.0256 1.0000 Uani . . . . . .
C18 C 0.2750(3) 0.7198(3) 0.47330(12) 0.0270 1.0000 Uani . . . . . .
C19 C 0.2013(3) 0.6583(3) 0.44478(12) 0.0346 1.0000 Uani . . . . . .
O20 O 0.3171(2) 0.7983(2) 0.45987(8) 0.0339 1.0000 Uani . . . . . .
C21 C 0.3689(3) 0.3617(3) 0.68219(12) 0.0249 1.0000 Uani . . . . . .
C22 C 0.4241(3) 0.3472(3) 0.72271(12) 0.0253 1.0000 Uani . . . . . .
C23 C 0.4873(3) 0.2616(3) 0.72880(12) 0.0266 1.0000 Uani . . . . . .
C24 C 0.4964(3) 0.1874(3) 0.69337(13) 0.0297 1.0000 Uani . . . . . .
C25 C 0.4427(3) 0.2028(3) 0.65355(13) 0.0313 1.0000 Uani . . . . . .
C26 C 0.3786(3) 0.2891(3) 0.64816(12) 0.0284 1.0000 Uani . . . . . .
O27 O 0.5446(2) 0.2416(2) 0.76702(9) 0.0346 1.0000 Uani . . . . . .
C28 C 0.5407(3) 0.3192(3) 0.80235(13) 0.0359 1.0000 Uani . . . . . .
C29 C 0.6180(4) 0.2899(4) 0.83835(17) 0.0566 1.0000 Uani . . . . . .
O30 O 0.5596(2) 0.1046(2) 0.70251(10) 0.0376 1.0000 Uani . . . . . .
C31 C 0.5765(4) 0.0347(4) 0.66559(16) 0.0550 1.0000 Uani . . . . . .
C36 C 0.4749(8) 0.5318(8) 0.0446(4) 0.1352 1.0000 Uani D . . . . .
C37 C 0.5577(7) 0.5855(6) 0.0219(3) 0.1129 1.0000 Uani D . . . . .
N6 N 0.3445(2) 0.5345(2) 0.64627(9) 0.0221 1.0000 Uani . . . . . .
H42 H 0.3183 0.5297 0.7353 0.0272 1.0000 Uiso R . . . . .
H41 H 0.2299 0.4433 0.7385 0.0271 1.0000 Uiso R . . . . .
H51 H 0.2372 0.4282 0.6583 0.0253 1.0000 Uiso R . . . . .
H142 H 0.1775 0.6995 0.4198 0.0500 1.0000 Uiso R . . . . .
H141 H 0.1435 0.6375 0.4633 0.0502 1.0000 Uiso R . . . . .
H143 H 0.2360 0.5976 0.4342 0.0502 1.0000 Uiso R . . . . .
H151 H 0.4345 0.8312 0.5177 0.0332 1.0000 Uiso R . . . . .
H161 H 0.5494 0.8696 0.5742 0.0340 1.0000 Uiso R . . . . .
H171 H 0.5577 0.7721 0.6411 0.0341 1.0000 Uiso R . . . . .
H221 H 0.3431 0.2975 0.6206 0.0309 1.0000 Uiso R . . . . .
H231 H 0.4483 0.1554 0.6298 0.0329 1.0000 Uiso R . . . . .
H261 H 0.6198 -0.0212 0.6762 0.0759 1.0000 Uiso R . . . . .
H263 H 0.6090 0.0698 0.6406 0.0760 1.0000 Uiso R . . . . .
H262 H 0.5109 0.0066 0.6560 0.0761 1.0000 Uiso R . . . . .
H281 H 0.4189 0.3968 0.7457 0.0281 1.0000 Uiso R . . . . .
H302 H 0.4723 0.3241 0.8152 0.0432 1.0000 Uiso R . . . . .
H301 H 0.5598 0.3859 0.7895 0.0430 1.0000 Uiso R . . . . .
H311 H 0.6235 0.3460 0.8596 0.0831 1.0000 Uiso R . . . . .
H313 H 0.5941 0.2282 0.8534 0.0831 1.0000 Uiso R . . . . .
H312 H 0.6844 0.2764 0.8242 0.0830 1.0000 Uiso R . . . . .
H321 H 0.1797 0.6469 0.7884 0.0571 1.0000 Uiso R . . . . .
H323 H 0.0691 0.6691 0.7698 0.0569 1.0000 Uiso R . . . . .
H322 H 0.0997 0.5572 0.7831 0.0571 1.0000 Uiso R . . . . .
H111 H 0.253(4) 0.635(4) 0.5211(14) 0.0297 1.0000 Uiso . . . . . .
O38 O 0.5951(12) 0.6724(11) 0.0394(6) 0.1911 0.5000 Uani D . . . . .
C35 C 0.4281(7) 0.4543(8) 0.0208(3) 0.1418 1.0000 Uani D . . . . .
C34 C 0.3418(12) 0.4012(13) 0.0397(6) 0.1752 0.5000 Uani D . . . . .
O33 O 0.2852(14) 0.3291(15) 0.0124(8) 0.1970 0.5000 Uani D . . . . .
O39 O 0.3048(15) 0.4311(15) 0.0793(9) 0.2207 0.5000 Uani D . . . . .
H371 H 0.5934 0.6391 0.0371 0.1482 0.5000 Uiso . . . . . .
H361 H 0.4628 0.5550 0.0747 0.1769 1.0000 Uiso . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . S1 . O3 . 117.40(16) yes
O2 . S1 . C4 . 108.6(2) yes
O3 . S1 . C4 . 108.41(19) yes
O2 . S1 . C5 . 109.53(16) yes
O3 . S1 . C5 . 108.85(16) yes
C4 . S1 . C5 . 103.07(18) yes
S1 . C4 . H321 . 113.2 no
S1 . C4 . H323 . 108.9 no
H321 . C4 . H323 . 109.0 no
S1 . C4 . H322 . 108.8 no
H321 . C4 . H322 . 109.3 no
H323 . C4 . H322 . 107.5 no
S1 . C5 . C6 . 113.7(2) yes
S1 . C5 . H42 . 107.7 no
C6 . C5 . H42 . 107.6 no
S1 . C5 . H41 . 108.0 no
C6 . C5 . H41 . 109.6 no
H42 . C5 . H41 . 110.3 no
C5 . C6 . C21 . 111.7(3) yes
C5 . C6 . N6 . 111.6(3) yes
C21 . C6 . N6 . 112.3(3) yes
C5 . C6 . H51 . 108.1 no
C21 . C6 . H51 . 106.4 no
N6 . C6 . H51 . 106.4 no
C8 . C7 . O11 . 128.9(3) yes
C8 . C7 . N6 . 106.4(3) yes
O11 . C7 . N6 . 124.6(3) yes
C7 . C8 . C9 . 108.3(3) yes
C7 . C8 . C13 . 129.6(3) yes
C9 . C8 . C13 . 122.1(3) yes
C8 . C9 . C10 . 107.7(3) yes
C8 . C9 . C16 . 122.5(3) yes
C10 . C9 . C16 . 129.8(3) yes
C9 . C10 . O12 . 128.7(3) yes
C9 . C10 . N6 . 107.0(3) yes
O12 . C10 . N6 . 124.4(3) yes
C8 . C13 . C14 . 116.0(3) yes
C8 . C13 . N17 . 118.4(3) yes
C14 . C13 . N17 . 125.6(3) yes
C13 . C14 . C15 . 121.1(3) yes
C13 . C14 . H151 . 119.5 no
C15 . C14 . H151 . 119.4 no
C14 . C15 . C16 . 122.5(3) yes
C14 . C15 . H161 . 118.2 no
C16 . C15 . H161 . 119.3 no
C15 . C16 . C9 . 115.8(3) yes
C15 . C16 . H171 . 121.3 no
C9 . C16 . H171 . 123.0 no
C13 . N17 . C18 . 128.7(3) yes
C13 . N17 . H111 . 119(3) no
C18 . N17 . H111 . 112(3) no
N17 . C18 . C19 . 113.9(3) yes
N17 . C18 . O20 . 123.2(3) yes
C19 . C18 . O20 . 122.9(3) yes
C18 . C19 . H142 . 110.0 no
C18 . C19 . H141 . 108.8 no
H142 . C19 . H141 . 110.0 no
C18 . C19 . H143 . 108.7 no
H142 . C19 . H143 . 110.7 no
H141 . C19 . H143 . 108.6 no
C6 . C21 . C22 . 122.1(3) yes
C6 . C21 . C26 . 119.1(3) yes
C22 . C21 . C26 . 118.8(3) yes
C21 . C22 . C23 . 121.1(3) yes
C21 . C22 . H281 . 119.2 no
C23 . C22 . H281 . 119.7 no
C22 . C23 . C24 . 119.4(3) yes
C22 . C23 . O27 . 125.0(3) yes
C24 . C23 . O27 . 115.6(3) yes
C23 . C24 . C25 . 119.2(3) yes
C23 . C24 . O30 . 115.4(3) yes
C25 . C24 . O30 . 125.4(3) yes
C24 . C25 . C26 . 120.7(3) yes
C24 . C25 . H231 . 120.4 no
C26 . C25 . H231 . 119.0 no
C25 . C26 . C21 . 120.9(3) yes
C25 . C26 . H221 . 118.7 no
C21 . C26 . H221 . 120.4 no
C23 . O27 . C28 . 116.3(3) yes
O27 . C28 . C29 . 108.1(3) yes
O27 . C28 . H302 . 111.1 no
C29 . C28 . H302 . 110.4 no
O27 . C28 . H301 . 108.9 no
C29 . C28 . H301 . 109.2 no
H302 . C28 . H301 . 109.1 no
C28 . C29 . H311 . 108.6 no
C28 . C29 . H313 . 108.6 no
H311 . C29 . H313 . 110.5 no
C28 . C29 . H312 . 109.2 no
H311 . C29 . H312 . 110.5 no
H313 . C29 . H312 . 109.4 no
C24 . O30 . C31 . 115.7(3) yes
O30 . C31 . H261 . 108.2 no
O30 . C31 . H263 . 110.7 no
H261 . C31 . H263 . 110.4 no
O30 . C31 . H262 . 109.1 no
H261 . C31 . H262 . 108.8 no
H263 . C31 . H262 . 109.6 no
C37 . C36 . C35 . 116.3(9) yes
C37 . C36 . H361 . 113.9 no
C35 . C36 . H361 . 129.7 no
C36 . C37 . C37 7_555 120.0(5) yes
C36 . C37 . O38 . 119.8(2) yes
C37 7_555 C37 . O38 . 119.1(6) yes
C36 . C37 . H371 . 119.6 no
C37 7_555 C37 . H371 . 120.3 no
O38 . C37 . H371 . 10.9 no
C6 . N6 . C10 . 125.2(3) yes
C6 . N6 . C7 . 123.7(3) yes
C10 . N6 . C7 . 110.6(3) yes
C36 . C35 . C35 7_555 123.6(6) yes
C36 . C35 . C34 . 120.0(7) yes
C35 7_555 C35 . C34 . 116.2(5) yes
C35 . C34 . O33 . 119.7(8) yes
C35 . C34 . O39 . 119.2(5) yes
O33 . C34 . O39 . 120.2(2) yes
C34 . O33 . O33 7_555 116.9(14) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . O2 . 1.441(3) yes
S1 . O3 . 1.447(3) yes
S1 . C4 . 1.757(4) yes
S1 . C5 . 1.768(3) yes
C4 . H321 . 0.952 no
C4 . H323 . 0.959 no
C4 . H322 . 0.959 no
C5 . C6 . 1.527(4) yes
C5 . H42 . 0.975 no
C5 . H41 . 0.974 no
C6 . C21 . 1.526(5) yes
C6 . N6 . 1.472(4) yes
C6 . H51 . 0.977 no
C7 . C8 . 1.486(5) yes
C7 . O11 . 1.222(4) yes
C7 . N6 . 1.396(4) yes
C8 . C9 . 1.384(5) yes
C8 . C13 . 1.390(5) yes
C9 . C10 . 1.480(5) yes
C9 . C16 . 1.373(5) yes
C10 . O12 . 1.224(4) yes
C10 . N6 . 1.400(4) yes
C13 . C14 . 1.403(5) yes
C13 . N17 . 1.398(4) yes
C14 . C15 . 1.383(5) yes
C14 . H151 . 0.933 no
C15 . C16 . 1.401(5) yes
C15 . H161 . 0.934 no
C16 . H171 . 0.933 no
N17 . C18 . 1.371(5) yes
N17 . H111 . 0.77(5) no
C18 . C19 . 1.497(5) yes
C18 . O20 . 1.216(5) yes
C19 . H142 . 0.960 no
C19 . H141 . 0.963 no
C19 . H143 . 0.955 no
C21 . C22 . 1.403(5) yes
C21 . C26 . 1.378(5) yes
C22 . C23 . 1.385(5) yes
C22 . H281 . 0.935 no
C23 . C24 . 1.421(5) yes
C23 . O27 . 1.371(4) yes
C24 . C25 . 1.377(6) yes
C24 . O30 . 1.371(4) yes
C25 . C26 . 1.397(5) yes
C25 . H231 . 0.931 no
C26 . H221 . 0.938 no
O27 . C28 . 1.445(4) yes
C28 . C29 . 1.505(6) yes
C28 . H302 . 0.962 no
C28 . H301 . 0.973 no
C29 . H311 . 0.959 no
C29 . H313 . 0.962 no
C29 . H312 . 0.968 no
O30 . C31 . 1.430(5) yes
C31 . H261 . 0.965 no
C31 . H263 . 0.962 no
C31 . H262 . 0.964 no
C36 . C37 . 1.438(13) yes
C36 . C35 . 1.363(14) yes
C36 . H361 . 0.949 no
C37 . C37 7_555 1.386(16) yes
C37 . O38 . 1.327(8) yes
C37 . H371 . 0.946 no
C35 . C35 7_555 1.32(2) yes
C35 . C34 . 1.421(9) yes
C34 . O33 . 1.43(2) yes
C34 . O39 . 1.32(3) yes
O33 . O33 7_555 1.09(4) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C5 . H42 . O12 . 124 0.98 2.44 3.093(7) yes
C5 . H42 . O12 5_666 141 0.98 2.33 3.152(7) yes
C5 . H41 . O20 8_546 171 0.97 2.49 3.453(7) yes
C14 . H151 . O20 . 121 0.93 2.32 2.910(7) yes
C26 . H221 . O3 8_546 138 0.94 2.52 3.276(7) yes
C26 . H221 . O38 3_665 132 0.94 2.55 3.261(7) yes
C25 . H231 . O2 8_546 165 0.93 2.44 3.349(7) yes
C31 . H261 . O20 2_645 169 0.97 2.54 3.493(7) yes
C22 . H281 . O12 5_666 179 0.94 2.43 3.366(7) yes
C4 . H321 . O3 5_666 149 0.95 2.54 3.392(7) yes
C4 . H323 . O11 2_555 126 0.96 2.37 3.042(7) yes
N17 . H111 . O11 . 133(4) 0.770 2.396 2.976(7) yes
